TY - JOUR AU - Emmetiere, Fabien; Grenning, Alexander J. TI - Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation SN - 0039-7881 SN - 1437-210X PY - 2020 JO - Synthesis JF - Synthesis LA - EN VL - 52 IS - 20 SP - 3077 EP - 3085 ET - 2020/07/21 DA - 2020/10/01 KW - Knoevenagel adducts KW - malononitriles KW - oxidative decyanation KW - redox processes KW - terpenoid synthesis AB - Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process involving alkylidene reduction, malononitrile oxidation, and acylcyanide reduction where molecular oxygen and NaBH4 work cooperatively. The method was applied to a variety of carbon skeletons and was utilized to synthesize complex terpenoid architectures. PB - © Georg Thieme Verlag DO - 10.1055/s-0040-1707184 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0040-1707184 ER -